US457863A - Georges de laire - Google Patents
Georges de laire Download PDFInfo
- Publication number
- US457863A US457863A US457863DA US457863A US 457863 A US457863 A US 457863A US 457863D A US457863D A US 457863DA US 457863 A US457863 A US 457863A
- Authority
- US
- United States
- Prior art keywords
- isoeugenol
- laire
- georges
- eugenol
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 13
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 13
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 13
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 10
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 5
- 239000005770 Eugenol Substances 0.000 description 5
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 5
- 229960002217 eugenol Drugs 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 3
- 244000223014 Syzygium aromaticum Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 3
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 3
- 235000012141 vanillin Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VHVOLFRBFDOUSH-NSCUHMNNSA-N Isosafrole Chemical compound C\C=C\C1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-NSCUHMNNSA-N 0.000 description 1
- VHVOLFRBFDOUSH-UHFFFAOYSA-N Isosafrole Natural products CC=CC1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
Definitions
- My invention relates to the preparation of isoeugenol direct from eugenol or essence of cloves, the product being destined, primarily, for utilization in the production of vanillin. This conversion or utilization of the isoeugenol has, however, nothing to do with my present application.
- isoeugenol was obtained for the first time by Messieurs Tiernann and Kraaz as a product of homoferulic acid; but this acid can only be obtained synthetically from vanillin, and it naturally follows that it cannot be employed as a basis for an industrial preparation of isoeugenol.
- the endeavors to obtain directly isoeugenol by means of the process which allows of the transformation of safrol into isosafrol have not given practical results, as shown by the recent publications of Messrs. Ciamician and Eyckmann.
- the process which constitutes the present invention allows of the ready preparation of the isoeugenol by means of eugenol or the essence of cloves, a substance which is readily obtained in commerce.
- I proceed as follows: I take about five hundred grams of eugenol, about twelve hundred and fifty grams of hydrate of potassa, and about two thousand five hundred grams of alcohol. These are heated to the boiling-point in an apparatus provided with a cohobater. The duration of the heating should be from sixteen to twenty-four hours, at the end of which time the reaction will be complete.
- the alcohol preferably amylic alcohol-will now be driven off by means of a current of steam, and the isoeugenol separated by treating the mass with dilute sulphuric or hydric-chloro acid.
- the isoeugenol separates from the mass as an oily substance, which may be collected by decantation. After having been thoroughly washed itis submitted to distillation for purification. It boils at from 252 to 262 centigrade.
- isoeugenol may be '6o utilized for the production of vanillin, and it may also be employed as a perfume. Having thus described my invention, I
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES GEORGES DE LAIRE,
PATENT OFFICE.
OF PARIS, FRANCE.
PROCESS OF MAKING ISOEUGENOL.
SPECIFICATION forming part of Letters Patent No. 457,863, dated August 18, 1891. Application filed December 3, 1890. Serial No. 37 3,429. (No specimens.) Patented in England November 1, 1890 No. 17,547.
To all whom it may concern.-
Be it known that I, GEORGES DE LAIRE, a citizen of the French Republic, residing'in Paris, France, have invented an Improved Method of Preparing Isoeugenol from Eugenol, (for which a patenthas been granted in Great Britain, No. 17 ,547, dated November 1, 1890,) of which the following is a specification.
My invention relates to the preparation of isoeugenol direct from eugenol or essence of cloves, the product being destined, primarily, for utilization in the production of vanillin. This conversion or utilization of the isoeugenol has, however, nothing to do with my present application.
I will proceed to explain how I carry out my invention in practice. isoeugenol was obtained for the first time by Messieurs Tiernann and Kraaz as a product of homoferulic acid; but this acid can only be obtained synthetically from vanillin, and it naturally follows that it cannot be employed as a basis for an industrial preparation of isoeugenol. The endeavors to obtain directly isoeugenol by means of the process which allows of the transformation of safrol into isosafrol have not given practical results, as shown by the recent publications of Messrs. Ciamician and Eyckmann.
The process which constitutes the present invention allows of the ready preparation of the isoeugenol by means of eugenol or the essence of cloves, a substance which is readily obtained in commerce.
In carrying out my invention I proceed as follows: I take about five hundred grams of eugenol, about twelve hundred and fifty grams of hydrate of potassa, and about two thousand five hundred grams of alcohol. These are heated to the boiling-point in an apparatus provided with a cohobater. The duration of the heating should be from sixteen to twenty-four hours, at the end of which time the reaction will be complete. The alcohol preferably amylic alcohol-will now be driven off by means of a current of steam, and the isoeugenol separated by treating the mass with dilute sulphuric or hydric-chloro acid. The isoeugenol separates from the mass as an oily substance, which may be collected by decantation. After having been thoroughly washed itis submitted to distillation for purification. It boils at from 252 to 262 centigrade.
As before stated, the isoeugenol may be '6o utilized for the production of vanillin, and it may also be employed as a perfume. Having thus described my invention, I
claim The herein-described method of preparing isoeugenol, which consists in first heating eugenol or essence of cloves, combined with hydrate of potassa and alcohol in about the proportions specified, until a reaction is effected, then expelling the alcohol with steam, and then treating the mass with acid, as described, in order to separate the isoeugenol therefrom, as set forth.
In witness whereof I have hereunto signed my name in the presence of two subscribing witnesses.
GEORGES DE LAIRE. Witnesses:
J. ARMENGAUD, J eune, R. M. HooPER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US457863A true US457863A (en) | 1891-08-18 |
Family
ID=2526738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US457863D Expired - Lifetime US457863A (en) | Georges de laire |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US457863A (en) |
-
0
- US US457863D patent/US457863A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2348683A (en) | Separation of di-isopropyl amine from isopropyl alcohol | |
| US2917537A (en) | Its esters | |
| US2955138A (en) | Process for the preparation of menthane diamine | |
| US2116439A (en) | Cyclic oxides and their preparation | |
| US2977291A (en) | Purification of glycerol | |
| US1921717A (en) | Method of making dichloroacetic acid | |
| US3094559A (en) | Method for the preparation of diphenylphosphinous chloride | |
| US2215472A (en) | Oxidation of hydrocarbons | |
| SU119184A1 (en) | The method of obtaining 1, 4, 5, 6, 7, 7-hexachlorobicyclo- (2, 2, 1) -5-heptene-2, 3-dicarboxylic anhydride | |
| US775251A (en) | Process of making homologues of ionone. | |
| US583719A (en) | Johann carl wilhelm ferdinand tiemann | |
| US1304108A (en) | Process for the manufacture of monochloracetic acid. | |
| US519693A (en) | Julius bertram | |
| US3043883A (en) | Manufacture of resorcinol | |
| SU123150A1 (en) | The method of obtaining ammonium nitrate under pressure | |
| US2769007A (en) | Manufacture of a pyridine homologue | |
| US2208296A (en) | Process of obtaining vinyl methyl ketone | |
| DE817306C (en) | Process for the preparation of 2, 7-dimethylocten- (2) -ol- (7) | |
| DE730236C (en) | Process for the catalytic decomposition of diphenyl ether to phenol | |
| US2513534A (en) | Purification of cyclopentanone | |
| US2411802A (en) | Purification of amine reaction mixtures | |
| US2455159A (en) | Purification of tetrasydbofuefuryl | |
| US1306710A (en) | Hiroshi nomtjra | |
| US1975843A (en) | Purification and hydrogenation of pyridines | |
| DE2745873C3 (en) | Process for the preparation of 1-cyano-1,3-butadiene |